Hydrochloric Acid → (3S)-1-(4-fluorobenzoyl)piperidine-3-carboxylic acid

HRID 1661178Notes

Reaction equation

HRID 1661178 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([C:8]([OH:10])=[O:9])[CH2:3]1.C(N(CC)CC)C.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.Cl>ClCCl>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:2]2[CH2:7][CH2:6][CH2:5][C@H:4]([C:8]([OH:10])=[O:9])[CH2:3]2)=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 24820453(3S)-piperidine-3-carboxylic acid hydrochloride

Product 1

HCID 858671(3S)-1-(4-fluorobenzoyl)piperidine-3-carboxylic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (S)-piperidine-3-carboxylic acid hydrochloride (0.75 g, 4.53 mmol) in dry dichloromethane (30 mL), triethylamine (1.97 mL, 14.0 mmol) and 4-fluorobenzoyl chloride (543 mL, 4.53 mmol) were added dropwise at 0° C. The resulting solution was kept under stiffing overnight at room temperature, under nitrogen atmosphere, then HCl 1N (30 mL) was added and the phases were separated. The organic layer was washed with HCl 1N (30 mL), with water (30 mL), dried over Na2SO4 and evaporated under reduced pressure to provide 1.05 g of 1-(4-fluoro-benzoyl)-(S)-piperidine-3-carboxylic acid as a yellow oil, used for the next step without further purification.

Workup

  1. additionwere added dropwise at 0° C
  2. customthe phases were separated
  3. washThe organic layer was washed with HCl 1N (30 mL), with water (30 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ce8cc8bb63e0429abf6f79360be2dc9f
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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